CN104640848A - Anthracene derivative and organic electroluminescent element using same - Google Patents

Anthracene derivative and organic electroluminescent element using same Download PDF

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CN104640848A
CN104640848A CN201480002297.3A CN201480002297A CN104640848A CN 104640848 A CN104640848 A CN 104640848A CN 201480002297 A CN201480002297 A CN 201480002297A CN 104640848 A CN104640848 A CN 104640848A
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replacement
carbon number
replace
compound
synthesis
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CN104640848B (en
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伊藤裕胜
齐藤博之
水木由美子
河村昌宏
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Idemitsu Kosan Co Ltd
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Abstract

The present invention relates to an anthracene derivative represented by the following formula (1). In the formula (1), L1The connecting group is selected from a single bond and a connecting group, and the connecting group is selected from a group formed by connecting 2-valent arylene, 2-valent heterocyclic group and 2-4 2-valent arylene and/or 2-valent heterocyclic group. Ar 1Selected from the following formulae (2) and (3). In the formulas (2) and (3), X is selected from an oxygen atom and a sulfur atom. In the formula (2), R11～R14Is used for with L1And (4) bonding. In the formula (3), R21～R24Is used for with L1And (4) bonding. Ar (Ar)2Selected from substituted or unsubstituted aryl with 6-50 carbon atoms in the ring and substituted or unsubstituted heterocyclic group with 5-50 carbon atoms in the ring.

Description

Anthracene derivant and use its organic electroluminescent device
Technical field
The present invention relates to anthracene derivant, use its organic electroluminescent device and comprise its electronics.
Background technology
Organic electroluminescent (EL) element is given expectation as the purposes of the full-color display element of big area of the low price of solid luminescence type, develops in a large number.As a rule, organic EL is made up of luminescent layer and a pair opposite electrode clipping this layer.If apply electric field between two electrodes, then inject electronics, from anode side injected hole from cathode side.And then this electronics is combined with hole at luminescent layer again, generates excited state, release energy in the form of light when excited state turns back to ground state.
The driving voltage compared with inorganic light-emitting diode of organic EL is in the past high, luminosity and luminous efficiency also low.In addition, deterioration in characteristics significantly and does not reach practical.Although nearest organic EL is improved gradually, but still require to improve luminous efficiency etc. further.
By improveing organic EL luminescent material, the performance of organic EL improves gradually.The raising of the luminous efficiency of organic EL is the important topic relevant to the raising of the reduction of the power consumption of indicating meter, weather resistance.So far be improved by many ways discussing, but still need improvement further.
In order to address these problems, in patent documentation 1 ~ 6, disclose the organic EL anthracene derivant with diphenylene-oxide alternatively base being used for luminescent material.
In addition, in patent documentation 4,7 ~ 11, disclose the luminescent material with naphtho-cumarone or naphtho-thionaphthene structure, if use these materials, the raising of luminous efficiency can be seen, but need further high efficiency.
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 11-111460 publication
Patent documentation 2: Japanese Unexamined Patent Publication 2005-314239 publication
Patent documentation 3: Japanese Unexamined Patent Publication 2007-63501 publication
Patent documentation 4: International Publication No. 06/128800 brochure
Patent documentation 5: International Publication No. 05/113531 brochure
Patent documentation 6: International Publication No. 08/143229 brochure
Patent documentation 7: International Publication No. 07/140847 brochure
Patent documentation 8: International Publication No. 08/6449 brochure
Patent documentation 9: International Publication No. 10/137285 brochure
Patent documentation 10: Japanese Unexamined Patent Application Publication 2012-503027 publication
Patent documentation 11: KR published patent 2012-0104067 publication
Summary of the invention
The object of the invention is to, provide and can manufacture low voltage and the material of high efficiency organic electroluminescent device.
According to a mode of the present invention, the anthracene derivant represented by following formula (1) can be provided.
[chemical formula 1]
[in formula (1), R 1~ R 8be selected from hydrogen atom respectively, halogen atom, hydroxyl, cyano group, replacement or the amino without replacement, replacement or the carbon number without replacement are the alkyl of 1 ~ 20, replacement or the carbon number without replacement are the alkoxyl group of 1 ~ 20, replacement or the carbon number without the formation ring replaced are the aryloxy of 6 ~ 30, replacement or the carbon number without the formation ring replaced are the arylthio of 6 ~ 30, replacement or the carbon number without replacement are the aIkylsilyl groups of 3 ~ 60, replacement or the carbon number without replacement are the arylsilyl groups of 8 ~ 60, replacement or the carbon number without the formation ring replaced are the aryl of 6 ~ 30, and replace or be the heterocyclic radical of 5 ~ 30 without the atomicity of formation ring replaced.
L 1be selected from singly-bound and linking group, the group that the heterocyclic radical of arylidene and/or divalent that described linking group is selected from the arylidene of divalent, the heterocyclic radical of divalent and 2 ~ 4 divalents connects and formed.
Ar 1be selected from following formula (2) and (3).
[chemical formula 2]
(in formula (2), (3), X is selected from Sauerstoffatom and sulphur atom.
In formula (2), R 11~ R 14in any one for L 1bonding.Not for L 1the R of bonding 11~ R 14and R 15~ R 20be selected from R respectively 1~ R 8the group of middle definition or atom.
In formula (3), R 21~ R 24in any one for L 1bonding.Not for L 1the R of bonding 21~ R 24and R 25~ R 30be selected from R respectively 1~ R 8the group of middle definition or atom.)
Ar 2be selected from replace or without the carbon number of formation ring replaced be 6 ~ 50 aryl and replacement or the atomicity without the formation ring replaced be the heterocyclic radical of 5 ~ 50.
R 1~ R 8, R 11~ R 20, R 21~ R 30, L 1and Ar 2in the adjacent optional bonding mutually of group and form ring.]
According to the present invention, can provide and can manufacture low voltage and the material of high efficiency organic electroluminescent device.
Embodiment
The anthracene derivant of a mode of the present invention is represented by following formula (1).
[chemical formula 3]
In formula (1), R 1~ R 8be selected from hydrogen atom respectively, halogen atom, hydroxyl, cyano group, replacement or the amino without replacement, replacement or the carbon number without replacement are the alkyl of 1 ~ 20, replacement or the carbon number without replacement are the alkoxyl group of 1 ~ 20, replacement or the carbon number without the formation ring replaced are the aryloxy of 6 ~ 30, replacement or the carbon number without the formation ring replaced are the arylthio of 6 ~ 30, replacement or the carbon number without replacement are the aIkylsilyl groups of 3 ~ 60, replacement or the carbon number without replacement are the arylsilyl groups of 8 ~ 60, replacement or the carbon number without the formation ring replaced are the aryl of 6 ~ 30, and replace or be the heterocyclic radical of 5 ~ 30 without the atomicity of formation ring replaced.
L 1be selected from singly-bound and linking group, the group that the heterocyclic radical of arylidene and/or divalent that linking group is selected from the arylidene of divalent, the heterocyclic radical of divalent and 2 ~ 4 divalents connects and formed.
Ar 1be selected from following formula (2) and (3).
[chemical formula 4]
In formula (2), (3), X is selected from Sauerstoffatom and sulphur atom.
In formula (2), R 11~ R 14in any one for L 1bonding.Not for L 1the R of bonding 11~ R 14and R 15~ R 20be selected from R respectively 1~ R 8the group of middle definition or atom.
In formula (3), R 21~ R 24in any one for L 1bonding.Not for L 1the R of bonding 21~ R 24and R 25~ R 30be selected from R respectively 1~ R 8the group of middle definition or atom.
Ar 2be selected from replace or without the carbon number of formation ring replaced be 6 ~ 50 aryl and replacement or the atomicity without the formation ring replaced be the heterocyclic radical of 5 ~ 50.
R 1~ R 8, R 11~ R 20, R 21~ R 30, L 1and Ar 2in the adjacent optional bonding mutually of group and form ring.
The substituting group represented by formula (2), (3) is the substituting group of the high efficiency contributing to organic EL described in patent documentation 9.The present invention finds, by the bonding position specialization by these substituting groups and anthracene skeleton, can play or its above luminous efficiency equal with patent documentation 9, realize lower voltage further simultaneously.
Above-claimed cpd is because the group that represented by formula (2) or (3) and anthracene skeleton are at specific position bonding, and based on the expansion of the planarity of molecule, intermolecular fillibility improves, and electron injection, transmittability improve.Therefore, for lower voltage, high efficiency can be realized during organic EL etc.
In addition, as the substituting group represented by formula (3), the substituting group represented by following formula (3 ') can be enumerated.
[chemical formula 5]
In formula (3 '), R 31~ R 34in any one for L 1bonding.Not for L 1the R of bonding 31~ R 34and R 35~ R 42be selected from R respectively 1~ R 8the group of middle definition or atom.
In formula (2), R 11~ R 14in preferred R 12or R 13for with L 1bonding.In formula (3), R 21~ R 24in preferred R 22or R 23for with L 1bonding.
That is, above-mentioned anthracene derivant is preferably represented by any one in following formula (4) ~ (7).
[chemical formula 6]
(in formula (4) ~ (7), R 1~ R 8, L 1, X, R 11~ R 20, R 21~ R 30and Ar 2identical with described formula (1).)
In addition, in formula (3 '), R 31~ R 34in preferred R 32or R 33for with L 1bonding.That is, above-mentioned anthracene derivant is preferably represented by any one in following formula (6 ') or (7 ').
[chemical formula 7]
(formula (6 ') and in (7 '), R 1~ R 8, L 1, X, R 31~ R 42and Ar 2identical with above-mentioned formula (1).)
In formula (1), Ar 2be preferably replacement or the aryl without replacement.
R 1~ R 8be preferably hydrogen atom.
L 1be preferably the arylidene of singly-bound or replacement or the divalent without replacement.
Formula (2), (3), in (3 '), X is preferably Sauerstoffatom.
In formula (2), not for L 1the R of bonding 11~ R 14and R 15~ R 20preferably be respectively hydrogen atom.
In formula (3), not for L 1the R of bonding 21~ R 24and R 25~ R 30preferably be respectively hydrogen atom.
In addition, in formula (3 '), not for L 1the R of bonding 31~ R 34and R 35~ R 42preferably be respectively hydrogen atom.
Above-mentioned anthracene derivant is preferably represented by any one in following formula (8) ~ (11).
[chemical formula 8]
(in formula (8) ~ (11), R 1~ R 8, X, R 11~ R 20, R 21~ R 30and Ar 2identical with above-mentioned formula (1).)
In addition, above-mentioned anthracene derivant is preferably represented by any one in following formula (12) ~ (15).
[chemical formula 9]
(in formula (12) ~ (15), R 1~ R 8, X, R 11~ R 20, R 21~ R 30and Ar 2identical with above-mentioned formula (1).)
In addition, above-mentioned anthracene derivant is preferably represented by any one in following formula (10 '), (11 '), (14 ') and (15 ').
[chemical formula 10]
(in formula (10 '), (11 '), (14 '), (15 '), R 1~ R 8, X, R 31~ R 42and Ar 2identical with above-mentioned formula (1).)
In this specification sheets, " forming the carbon of ring " refers to the carbon atom forming saturated rings, unsaturated ring or aromatic nucleus." form the atom of ring " and refer to the carbon atom and heteroatoms that form heterocycle (comprising saturated rings, unsaturated ring and aromatic nucleus).
In this specification sheets, " carbon number is a ~ b " in the statement that " replace or be the XX yl of a ~ b without the carbon number replaced " is such represents that XX group is without carbon number when replacing, substituent carbon number when not having a replacement containing XX group.
In addition, as the substituting group in " replace or without replace ", as long as no special description, the silyl, alkoxyl group, aryloxy, arylthio, aryl, heterocyclic radical, haloalkyl, hydroxyl, nitro, carboxyl, aralkyl etc. of halogen atom described later, cyano group, alkyl, cycloalkyl, silyl, replacement can be enumerated.
" without replacing " time " replace or without replace " refers to and is not replaced by described substituting group, and is bonded with hydrogen atom.
In the present invention, hydrogen atom comprises the different isotropic substance of neutron number, i.e. protium (protium), deuterium (deuterium) and tritium (tritium).
For the R in above-mentioned formula 1~ R 8, L 1, R 11~ R 20, R 21~ R 30, R 31~ R 42, Ar 2, and " replace or without replace " in each substituting group, describe in detail below.
As halogen atom, fluorine, chlorine, bromine, iodine etc. can be enumerated, preferred fluorine.As haloalkyl, methyl fluoride, difluoromethyl, trifluoromethyl, fluoro ethyl, trifluoromethyl etc. can be enumerated.
As amino, be expressed as-NHR w, or-N (R w) 2.As this R wexample, the carbon number can enumerating formation ring described later is the aryl of 6 ~ 30.Particularly preferably phenyl amino.
As carbon number be 1 ~ 20 (preferred carbon number is 1 ~ 10, more preferably carbon number be 1 ~ 8, particularly preferably carbon number be 1 ~ 4) alkyl, methyl, ethyl, propyl group, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl etc. can be enumerated.In addition, the alkyl that also can be replaced by aryl described later, that is, be combined with the substituting group (such as phenyl methyl, 2-propyloxy phenyl base etc.) of alkylidene group and aryl.
Above-mentioned carbon number is preferably 1 ~ 10, and more preferably 1 ~ 6.Wherein, preferable methyl, ethyl, propyl group, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, n-hexyl.
As cycloalkyl, be that to form the carbon number of ring be 3 ~ 20 cycloalkyl of (carbon number being preferably formed ring be 3 ~ 10, more preferably form the carbon number of ring be 3 ~ 8), can enumerate such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl, norcamphyl etc.
Carbon number be 1 ~ 20 (preferred carbon number is 1 ~ 10, more preferably carbon number be 1 ~ 8, particularly preferably carbon number be 1 ~ 4) alkoxyl group be the group represented by-OY, as the example of Y, the example same with above-mentioned alkyl can be enumerated.Alkoxyl group is such as methoxyl group, oxyethyl group.
Be 6 ~ 50 as forming the carbon number of the ring aryl of (carbon number being preferably formed ring is 6 ~ 30, more preferably formed the carbon number of ring is 6 ~ 20, particularly preferably to form the carbon number of ring be 6 ~ 12), can enumerate such as phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 6- base, 1-benzo [c] phenanthryl, 2-benzo [c] phenanthryl, 3-benzo [c] phenanthryl, 4-benzo [c] phenanthryl, 5-benzo [c] phenanthryl, 6-benzo [c] phenanthryl, 1-benzo [g] base, 2-benzo [g] base, 3-benzo [g] base, 4-benzo [g] base, 5-benzo [g] base, 6-benzo [g] base, 7-benzo [g] base, 8-benzo [g] base, 9-benzo [g] base, 10-benzo [g] base, 11-benzo [g] base, 12-benzo [g] base, 13-benzo [g] base, 14-benzo [g] base, 1-benzo [a] anthryl, 2-benzo [a] anthryl, 3-benzo [a] anthryl, 4-benzo [a] anthryl, 5-benzo [a] anthryl, 6-benzo [a] anthryl, 7-benzo [a] anthryl, 8-benzo [a] anthryl, 9-benzo [a] anthryl, 10-benzo [a] anthryl, 11-benzo [a] anthryl, 12-benzo [a] anthryl, 13-benzo [a] anthryl, 14-benzo [a] anthryl, 1-triphenyl, 2-triphenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, benzo fluorenyl, dibenzo fluorenyl, 2-xenyl, 3-xenyl, 4-xenyl, p-terphenyl base-4-base, p-terphenyl base-3-base, p-terphenyl base-2-base, meta-terphenyl base-4-base, meta-terphenyl base-3-base, meta-terphenyl base-2-base etc.
Be preferably phenyl, 1-naphthyl, 2-naphthyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 5-benzo [c] phenanthryl, 4-benzo [a] anthryl, 7-benzo [a] anthryl, 1-triphenyl, 2-triphenyl.
1-fluorenyl, 2-fluorenyl, 3-fluorenyl and 4-fluorenyl preferably replace on the carbon atom of 9 to be had: above-mentioned replacement or the carbon number without replacement are alkyl or the replacement of 1 ~ 20 or are the aryl of 6 ~ 18 without the carbon number replaced.
In this specification sheets, aryl (aromatic hydrocarbons) refers to the hydrocarbon be made up of the monocycle (non-condensed aryl) of display aromatic series or many rings (fused-aryl).
Fused-aryl refers to the group after the ring structure condensed ring in above-mentioned aryl more than 2 rings.Non-condensed aryl refers to the group in above-mentioned aryl except described fused-aryl.
As fused-aryl, be that to form the carbon number of ring be 10 ~ 50 fused-aryl of (carbon number being preferably formed ring be 10 ~ 30, more preferably form the carbon number of ring be 10 ~ 20), in the concrete example of above-mentioned aryl, such as 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl, 9-naphthacenyl, 1-pyrenyl, 2-pyrenyl, 4-pyrenyl, 6-can be enumerated base, 5-benzo [c] phenanthryl, 4-benzo [a] anthryl, 7-benzo [a] anthryl, 1-triphenyl, 2-triphenyl etc.
Be preferably 1-naphthyl, 2-naphthyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 5-benzo [c] phenanthryl, 4-benzo [a] anthryl, 7-benzo [a] anthryl, 1-triphenyl, 2-triphenyl.
As the arylidene of divalent, can enumerate and remove the group after 2 hydrogen atoms from above-mentioned aryl.
The aryloxy that to form the carbon number of ring be 6 ~ 30 (carbon number being preferably formed ring be 6 ~ 20, more preferably form the carbon number of ring be 6 ~ 12) is the group being expressed as-OAr.As the example of Ar, same with above-mentioned aryl.Aryloxy is such as phenoxy group.
The arylthio that to form the carbon number of ring be 6 ~ 30 (carbon number being preferably formed ring be 6 ~ 20, more preferably form the carbon number of ring be 6 ~ 12) refers to the group being expressed as-SAr.As the example of Ar, same with above-mentioned aryl.
Be that 5 ~ 50 (atomicity being preferably formed ring is 5 ~ 30 as forming the atomicity of ring, more preferably the atomicity forming ring is 5 ~ 30, the atomicity particularly preferably forming ring is 5 ~ 12) heterocyclic radical, such as 1-pyrryl can be enumerated, 2-pyrryl, 3-pyrryl, pyrazinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1-indyl, 2-indyl, 3-indyl, 4-indyl, 5-indyl, 6-indyl, 7-indyl, 1-pseudoindoyl, 2-pseudoindoyl, 3-pseudoindoyl, 4-pseudoindoyl, 5-pseudoindoyl, 6-pseudoindoyl, 7-pseudoindoyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-isobenzofuran-base, 3-isobenzofuran-base, 4-isobenzofuran-base, 5-isobenzofuran-base, 6-isobenzofuran-base, 7-isobenzofuran-base, 1-dibenzofuran group, 2-dibenzofuran group, 3-dibenzofuran group, 4-dibenzofuran group, 1-dibenzo thiophenyl, 2-dibenzo thiophenyl, 3-dibenzo thiophenyl, 4-dibenzo thiophenyl, quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazyl, 2-carbazyl, 3-carbazyl, 4-carbazyl, 9-carbazyl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridyl, 2-acridyl, 3-acridyl, 4-acridyl, 9-acridyl, 1,7-phenanthroline-2-base, 1,7-phenanthroline-3-base, 1,7-phenanthroline-4-base, 1,7-phenanthroline-5-base, 1,7-phenanthroline-6-base, 1,7-phenanthroline-8-base, 1,7-phenanthroline-9-base, 1,7-phenanthroline-10-base, 1,8-phenanthroline-2-base, 1,8-phenanthroline-3-base, 1,8-phenanthroline-4-base, 1,8-phenanthroline-5-base, 1,8-phenanthroline-6-base, 1,8-phenanthroline-7-base, 1,8-phenanthroline-9-base, 1,8-phenanthroline-10-base, 1,9-phenanthroline-2-base, 1,9-phenanthroline-3-base, 1,9-phenanthroline-4-base, 1,9-phenanthroline-5-base, 1,9-phenanthroline-6-base, 1,9-phenanthroline-7-base, 1,9-phenanthroline-8-base, 1,9-phenanthroline-10-base, 1,10-phenanthroline-2-base, 1,10-phenanthroline-3-base, 1,10-phenanthroline-4-base, 1,10-phenanthroline-5-base, 2,9-phenanthroline-1-base, 2,9-phenanthroline-3-base, 2,9-phenanthroline-4-base, 2,9-phenanthroline-5-base, 2,9-phenanthroline-6-base, 2,9-phenanthroline-7-base, 2,9-phenanthroline-8-base, 2,9-phenanthroline-10-base, 2,8-phenanthroline-1-base, 2,8-phenanthroline-3-base, 2,8-phenanthroline-4-base, 2,8-phenanthroline-5-base, 2,8-phenanthroline-6-base, 2,8-phenanthroline-7-base, 2,8-phenanthroline-9-base, 2,8-phenanthroline-10-base, 2,7-phenanthroline-1-base, 2,7-phenanthroline-3-base, 2,7-phenanthroline-4-base, 2,7-phenanthroline-5-base, 2,7-phenanthroline-6-base, 2,7-phenanthroline-8-base, 2,7-phenanthroline-9-base, 2,7-phenanthroline-10-base, 1-phenazinyl, 2-phenazinyl, 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl, lysivane base, 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl, 10-phenoxazinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furan a word used for translation base, 2-thienyl, 3-thienyl, 2-methylpyrrole-1-base, 2-methylpyrrole-3-base, 2-methylpyrrole-4-base, 2-methylpyrrole-5-base, 3-methylpyrrole-1-base, 3-methylpyrrole-2-base, 3-methylpyrrole-4-base, 3-methylpyrrole-5-base, 2-tertiary butyl pyrroles-4-base, 3-(2-phenyl propyl) pyrroles-1-base, 2-methyl isophthalic acid-indyl, 4-methyl isophthalic acid-indyl, 2-methyl-3-indyl, 4-methyl-3-indyl, the 2-tertiary butyl-1-indyl, the 4-tertiary butyl-1-indyl, the 2-tertiary butyl-3-indyl, the 4-tertiary butyl-3-indyl, 1-benzimidazolyl-, 2-benzimidazolyl-, 4-benzimidazolyl-, 5-benzimidazolyl-, 6-benzimidazolyl-, 7-benzimidazolyl-, 2-imidazo [1,2-a] pyridyl, 3-imidazo [1,2-a] pyridyl, 5-imidazo [1,2-a] pyridyl, 6-imidazo [1,2-a] pyridyl, 7-imidazo [1,2-a] pyridyl, 8-imidazo [1,2-a] pyridyl, 2-ketone benzimidaozole-1-base, 2-ketone benzimidaozole-3-base, 2-ketone benzimidaozole-4-base, 2-ketone benzimidaozole-5-base, 2-ketone benzimidaozole-6-base, 2-ketone benzimidaozole-7-base etc.
Be preferably 1-dibenzofuran group, 2-dibenzofuran group, 3-dibenzofuran group, 4-dibenzofuran group, 1-dibenzo thiophenyl, 2-dibenzo thiophenyl, 3-dibenzo thiophenyl, 4-dibenzo thiophenyl, 1-carbazyl, 2-carbazyl, 3-carbazyl, 4-carbazyl, 9-carbazyl, 1-benzimidazolyl-, 2-benzimidazolyl-, 4-benzimidazolyl-, 5-benzimidazolyl-, 6-benzimidazolyl-, 7-benzimidazolyl-, 2-imidazo [1,2-a] pyridyl, 3-imidazo [1,2-a] pyridyl, 5-imidazo [1,2-a] pyridyl, 6-imidazo [1,2-a] pyridyl, 7-imidazo [1,2-a] pyridyl, 8-imidazo [1,2-a] pyridyl 2-pyridyl, 3-pyridyl, 4-pyridyl, 1,10-phenanthroline-2-base, 1,10-phenanthroline-3-base, 1,10-phenanthroline-4-base, 1,10-phenanthroline-5-base, 2-ketone benzimidaozole-1-base, 2-ketone benzimidaozole-3-base, 2-ketone benzimidaozole-4-base, 2-ketone benzimidaozole-5-base, 2-ketone benzimidaozole-6-base, 2-ketone benzimidaozole-7-base, is particularly preferably 1-dibenzofuran group, 2-dibenzofuran group, 3-dibenzofuran group, 4-dibenzofuran group, 1-dibenzo thiophenyl, 2-dibenzo thiophenyl, 3-dibenzo thiophenyl, 4-dibenzo thiophenyl, 1-carbazyl, 2-carbazyl, 3-carbazyl, 4-carbazyl, 9-carbazyl.
Heterocyclic radical comprises the hetero-aromatic ring base of monocycle, multiple hetero-aromatic ring condense after assorted fused aromatic rings base and aromatic hydrocarbons ring and hetero-aromatic ring condense after assorted fused aromatic rings base.
As the annelated heterocycles base that the atomicity forming ring is 8 ~ 30 (being preferably formed the atomicity 8 ~ 20 of ring), in the concrete example of above-mentioned heterocyclic radical, such as dibenzofuran group, dibenzo thiophenyl and carbazyl etc. can be enumerated.
As the heterocyclic radical of divalent, the group removing 2 hydrogen atoms from above-mentioned heterocyclic radical can be enumerated.
The arylidene of divalent in the group that the arylidene of 2 ~ 4 divalents and/or the heterocyclic radical of divalent connect and formed and the heterocyclic radical of divalent are respectively above-mentioned group.As arylidene, be preferably selected from replacement or the phenylene without replacement, replacement or the naphthylidene without replacement, replacement or the phenanthrylene without replacement, replacement or the anthrylene without replacement, replacement or the sub-pyrenyl without replacement, replacement or the fluorenylidene without replacement, as heterocyclic radical, be preferably selected from replacement or the pyridylidene without replacement, replacement or the sub-pyrimidyl without replacement, replacement or the sub-pyrazinyl without replacement, replacement or the sub-pyridazinyl without replacement, replacement or the sub-triazinyl without replacement, replacement or the dibenzo furylidene without replacement, replacement or the sub-thiophenyl of dibenzo without replacement, replacement or the sub-carbazyl without replacement.
More preferably following structure.
[chemical formula 11]
The preferred structure of the anthracene derivant that the arylidene of 2 ~ 4 divalents and/or the heterocyclic radical of divalent connect and formed can enumerate such as following structure.
[chemical formula 12]
Be the aIkylsilyl groups of 3 ~ 60 as carbon number, the trialkylsilkl with the alkyl exemplified in abovementioned alkyl can be enumerated, trimethyl silyl can be enumerated specifically, triethylsilyl, three normal-butyl silyls, three n-octyl silyls, tri-iso-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyl n propylsilyl, dimethyl n butyl silyl, dimethyl-t-butylsilyl, diethyl isopropyl silyl, vinyldimethylsilyl, propyl-dimethyl silyl, triisopropyl silyl etc.3 alkyl can be identical or different respectively.
Be the arylsilyl groups of 8 ~ 60 as carbon number, arylsilyl groups, alkylaryl silyl, dialkyiarylsilyl, diarylsilyl, allcyldiaryl silyl, diarye silyl can be enumerated.Multiple aryl each other or alkyl each other can be identical or different.
Dialkyiarylsilyl can be enumerated such as has 2 alkyl exemplified in abovementioned alkyl and the dialkyiarylsilyl with 1 above-mentioned aryl.The carbon number of dialkyiarylsilyl is preferably 8 ~ 30.2 alkyl can be identical or different respectively.
Allcyldiaryl silyl can be enumerated such as has 1 alkyl exemplified in abovementioned alkyl and the allcyldiaryl silyl with 2 above-mentioned aryl.The carbon number of allcyldiaryl silyl is preferably 13 ~ 30.2 aryl can be identical or different respectively.
Diarye silyl can enumerate the diarye silyl such as with 3 above-mentioned aryl.The carbon number of diarye silyl is preferably 18 ~ 30.3 aryl can be identical or different respectively.
As such arylsilyl groups, such as phenyldimethylsilyl, diphenylmethylsilyl, diphenyl-t-butylsilyl, triphenyl-silyl can be enumerated.
Aralkyl is expressed as-Y-Z, and the example as Y can enumerate the example of the alkylidene group corresponding with the example of abovementioned alkyl, and the example as Z can enumerate the example of above-mentioned aryl.Preferred aralkyl to be carbon number be 7 ~ 50 aralkyl (carbon number of aryl moiety be 6 ~ 49 (preferably 6 ~ 30, more preferably 6 ~ 20, particularly preferably 6 ~ 12), moieties carbon number be 1 ~ 44 (preferably 1 ~ 30, more preferably 1 ~ 20, further preferably 1 ~ 10, particularly preferably 1 ~ 6)), such as benzyl, phenylethyl, 2-phenyl-propane-2-base.
The anthracene derivant of a mode of the present invention illustrates below, but is not limited to these.
[chemical formula 13]
[chemical formula 14]
[chemical formula 15]
[chemical formula 16]
[chemical formula 17]
[chemical formula 18]
[chemical formula 19]
[chemical formula 20]
[chemical formula 21]
[chemical formula 22]
[chemical formula 23]
[chemical formula 24]
[chemical formula 25]
[chemical formula 26]
[chemical formula 27]
[chemical formula 28]
[chemical formula 29]
[chemical formula 30]
[chemical formula 31]
[chemical formula 32]
[chemical formula 33]
[chemical formula 34]
[chemical formula 35]
[chemical formula 36]
* mark in table is illustrated respectively in the bonding position of anthracene nucleus.
[chemical formula 37]
* mark in table is illustrated respectively in the bonding position of anthracene nucleus.
[chemical formula 38]
[chemical formula 39]
[chemical formula 40]
[chemical formula 41]
[chemical formula 42]
[chemical formula 43]
[chemical formula 44]
[chemical formula 45]
[chemical formula 46]
[chemical formula 47]
[chemical formula 48]
[chemical formula 49]
[chemical formula 50]
[chemical formula 51]
[chemical formula 52]
[chemical formula 53]
[chemical formula 54]
[chemical formula 55]
[chemical formula 56]
[chemical formula 57]
[chemical formula 58]
[chemical formula 59]
[chemical formula 60]
[chemical formula 61]
[chemical formula 62]
[chemical formula 63]
[chemical formula 64]
[chemical formula 65]
[chemical formula 66]
[chemical formula 67]
[chemical formula 68]
[chemical formula 69]
[chemical formula 70]
[chemical formula 71]
[chemical formula 72]
[chemical formula 73]
[chemical formula 74]
[chemical formula 75]
[chemical formula 76]
[chemical formula 77]
Above-mentioned anthracene derivant can be used as organic EL material, organic EL luminescent material.
In organic electroluminescent (EL) element of a mode of the present invention, between negative electrode and positive electrode, have the organic thin film layer of more than one deck comprising luminescent layer, at least one deck of organic thin film layer contains separately or contains above-mentioned anthracene derivant as the ingredients of a mixture.
For above-mentioned organic EL, preferred luminescent layer contains above-mentioned anthracene derivant.Preferred above-mentioned anthracene derivant is the material of main part of luminescent layer.
Be the organic EL of multi-layered type as organic thin film layer, can enumerate with the stacked element of the structure such as (anode/hole injection layer/luminescent layer/negative electrode), (anode/luminescent layer/electron injecting layer/negative electrode), (anode/hole injection layer/luminescent layer/electron injecting layer/negative electrode), (anode/hole injection layer/hole transmission layer/luminescent layer/electron injecting layer/negative electrode).
In addition, in above-mentioned organic EL, above-mentioned anthracene derivant may be used for above-mentioned arbitrary organic layer, but preferably is contained in light-emitting zone.Particularly preferably be included in luminescent layer.Content is generally 30 ~ 100 % by mole.
Organic EL is multilayered structure by making described organic thin film layer, the brightness that can prevent quenches causes and the reduction in life-span.If needed, luminescent material, dopant material, hole-injecting material and electron injection material can be combinationally used.In addition, by dopant material, luminosity, luminous efficiency sometimes can be made to improve.In addition, hole injection layer, luminescent layer, electron injecting layer can be formed by two-layer above Rotating fields respectively.Now, when hole injection layer, the layer from electrode injection hole is called hole injection layer, hole will be accepted from hole injection layer and hole transport to the layer of luminescent layer is called hole transmission layer.Similarly, when electron injecting layer, the layer from electrode injection electronics is called electron injecting layer, electronics will be accepted from electron injecting layer and by electric transmission to luminescent layer layer be called electron transfer layer.These each layers based on the energy level of material, thermotolerance, with the adaptation of organic layer or metal electrode etc. respectively because of usually choice for use.
As the material that can use in luminescent layer together with above-mentioned anthracene derivant, can enumerate such as naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, decacyclene, coronene, tetraphenyl cyclopentadiene, Pentaphenylcyclopentadiene, fluorenes, condensed polycyclc aromatic compound and their derivatives such as spiral shell fluorenes, the organometallic complexs such as three (8-quinoline) aluminium, triarylamine derivatives, styryl sulfonamide derivatives, stilbene derivatives, coumarin derivatives, pyran derivate, oxazinone derivative, benzothiazole derivant, benzoxazole derivative, benzimidizole derivatives, pyrazines derivatives, cinnamate derivates, Diketopyrrolopyrrolederivative derivative, acridone derivatives, quinacridone derivative etc., but be not limited to these.
In above-mentioned organic EL, except above-mentioned luminescent material, luminous doping agent (phosphorescent dopant and/or fluorescence doping agent) can also be contained as required in luminescent layer.In addition, can on the luminescent layer comprising above-claimed cpd, the stacked luminescent layer comprising these doping agents.
Fluorescence doping agent is can by the compound of singlet exciton luminescence.As fluorescence doping agent, be preferably the compound that the illuminant colour required by combining is selected from chelate complexes, coumarin derivatives, tetraphenylbutadiene derivative, bisstyryl arylene derivatives, the oxadiazole derivatives etc. such as amine compound, aromatics, three (8-quinoline) aluminium complex, more preferably styrylamine compounds, styryl diamine compound, novel arylamine compound, aryl diamine compound, further preferred fused polycycle sulfonamide derivatives.These fluorescence doping agents can be used alone or combine multiple use.
As fused polycycle sulfonamide derivatives, the material preferably represented by following formula (20).
[chemical formula 78]
In formula (20), Y represents that replacement or the carbon number without the formation ring replaced are the fused aromatic alkyl of 10 ~ 50.
Ar 101, Ar 102represent respectively and replace or be the aryl of 6 ~ 50 without the carbon number of formation ring replaced or replace or atomicity without the formation ring replaced is the heterocyclic radical of 5 ~ 50.
As the concrete example of Y, above-mentioned fused-aryl can being enumerated, preferably to replace or without the anthryl replaced, replacement or without the pyrenyl replaced, replacement or without replacing base.
N is the integer of 1 ~ 4.N is preferably the integer of 1 ~ 2.
Above-mentioned formula (20) is preferably represented by following formula (21) ~ (24).
[chemical formula 79]
In formula (21) ~ (24), R e, R fand R grepresent that replacement or the carbon number without replacement are the alkyl of 1 ~ 20 respectively, replacement or the carbon number without replacement are the thiazolinyl of 2 ~ 50, replacement or the carbon number without replacement are the alkynyl of 2 ~ 50, replacement or the carbon number without replacement are the aralkyl of 1 ~ 20, replacement or the carbon number without the formation ring replaced are the cycloalkyl of 3 ~ 20, replacement or the carbon number without replacement are the alkoxyl group of 1 ~ 20, replacement or the carbon number without the formation ring replaced are the aryloxy of 6 ~ 20, replacement or the carbon number without the formation ring replaced are the aryl of 6 ~ 50, replacement or the silyl without replacement, replace or without replace carbon number be 1 ~ 50 alkyl germanium base, replace or without the carbon number of formation ring replaced be 6 ~ 50 aryl germanium base.R e, R fand R gany bonding position of the phenyl ring forming fused polycycle skeleton can be bonded to respectively.
R e, R fand R gpreference be replace or be the aryl of 6 ~ 50 without the carbon number of formation ring replaced, be more preferably and replace or without the phenyl replaced, replacement or without the naphthyl etc. replaced.
T represents the integer of 0 ~ 10.U represents the integer of 0 ~ 8.M represents the integer of 0 ~ 10.
Ar 201~ Ar 218represent respectively and replace or be the aryl of 6 ~ 50 without the carbon number of formation ring replaced or replace or atomicity without the formation ring replaced is the heterocyclic radical of 5 ~ 50.
Ar 201~ Ar 218preference be replace or without replace phenyl, replacement or without replace dibenzofuran group etc.Ar 201~ Ar 218substituent preference be alkyl, cyano group, replacement or without replace silyl.
In formula (21) ~ (24), as the example of alkyl, alkoxyl group, aryl, aryloxy, heterocyclic radical, above-mentioned illustrative group can be enumerated.
Be that 2 ~ 50 (preferred carbon number is 2 ~ 30 as carbon number, more preferably carbon number is 2 ~ 20, particularly preferably carbon number is 2 ~ 10) thiazolinyl, vinyl can be enumerated, allyl group, 1-butylene base, crotyl, 3-butenyl, 1, 3-butadienyl, 1-methyl ethylene, styryl, 2, 2-diphenylacetylene, 1, 2-diphenylacetylene, 1-methacrylic, 1, 1-dimethyl-allyl, 2-methacrylic, 1-phenyl allyl, 2-phenyl allyl, 3-phenyl allyl, 3, 3-phenylbenzene allyl group, 1, 2-dimethyl-allyl, 1-phenyl-1-butylene base, 3-phenyl-1-butylene base etc., preferably can enumerate styryl, 2, 2-diphenylacetylene, 1, 2-diphenylacetylene etc.
As carbon number be 2 ~ 50 (preferred carbon number is 2 ~ 30, more preferably carbon number be 2 ~ 20, particularly preferably carbon number be 2 ~ 10) alkynyl, proyl, 3-pentynyl etc. can be enumerated.
As alkyl germanium base, methyl hydrogen germyl, trimethylgermyl groups, triethyl germyl, tripropyl germyl, dimethyl tertiary butyl germyl etc. can be enumerated.
As aryl germanium base, phenyl dihydro germyl, phenylbenzene hydrogen germyl, triphenyl germyl, trimethylphenyl germyl, three naphthyl germyls etc. can be enumerated.
As styrylamine compounds and styryl diamine compound, the compound represented by following formula (17) and (18) can be enumerated.
[chemical formula 80]
In formula (17), Ar 301for the group of k valency, be the group of the k valency corresponding with phenyl, naphthyl, xenyl, terphenyl, stilbene radicals, styryl aryl, diphenylethyllene aryl, Ar 302and Ar 303being respectively the carbon number forming ring is the aryl of 6 ~ 20, Ar 301, Ar 302and Ar 303can be substituted.
K is the integer of 1 ~ 4, and wherein k is preferably the integer of 1 ~ 2.Ar 301~ Ar 303in any one be group containing styryl.And preferred Ar 302or Ar 303at least one replaced by styryl.
At this, the carbon number as formation ring is the aryl of 6 ~ 20, can enumerate above-mentioned aryl specifically, can preferably enumerate phenyl, naphthyl, anthryl, phenanthryl, terphenyl etc.
In formula (18), Ar 304~ Ar 306for the replacement of v valency or the carbon number without the formation ring replaced are the aryl of 6 ~ 40.V is the integer of 1 ~ 4, and wherein v is preferably the integer of 1 ~ 2.
At this, the carbon number as the formation ring in formula (18) is the aryl of 6 ~ 40, can enumerate above-mentioned aryl specifically, preferred naphthyl, anthryl, base, pyrenyl or by the aryl shown in formula (20).
It should be noted that, as the preferred substituents that described aryl replaces, can enumerate carbon number be 1 ~ 6 the aryl that alkyl, carbon number are the alkoxyl group of 1 ~ 6, the carbon number that forms ring is the aryl of 6 ~ 40, the carbon number that is formed ring is 6 ~ 40 replace amino, there is ester group that the carbon number forming ring is the aryl of 5 ~ 40, there is ester group, cyano group, nitro, halogen atom etc. that carbon number is the alkyl of 1 ~ 6.
As hole-injecting material, preferably there is the ability of transporting holes, inject effect from the hole of anode, there is excellent hole injection effect and the compound of film Forming ability excellence for luminescent layer or luminescent material.Specifically, phthalocyanine derivates, naphthalocyanine derivative, derivatives of porphyrin, benzidine type triphenylamine, diamine type triphenylamine, six cyano group six azepine triphenylenes etc. and the macromolecular material such as their derivative and Polyvinyl carbazole, polysilane, electroconductive polymer can be enumerated, but be not limited to these.
In the hole-injecting material that can be used in above-mentioned organic EL, more effective hole-injecting material is phthalocyanine derivates.
As phthalocyanine (Pc) derivative, such as, there are phthalocyanine derivates and the naphthalocyanine derivative such as H2Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl2SiPc, (HO) AlPc, (HO) GaPc, VOPc, TiOPc, MoOPc, GaPc-O-GaPc, but are not limited to these.
In addition, accepting electron species by adding TCNQ derivative etc. in hole-injecting material, carrier sensitization can also be made.
The preferred hole mobile material that can use in above-mentioned organic EL is aromatic nitrile base derivative.
As aromatic nitrile base derivative, be such as N, N '-phenylbenzene-N, N '-dinaphthyl-1,1 '-xenyl-4,4 '-diamines, N, N, N ', N '-tetrad phenyl-1,1 '-xenyl-4,4 '-diamines etc. or there is oligopolymer or the polymer of these aromatic nitrile base skeletons, but be not limited to these.
As electron injection material, preferably have the ability of transmission electronic, from negative electrode electron injection effect, there is excellent electron injection effect and the compound of film Forming ability excellence for luminescent layer or luminescent material.
In above-mentioned organic EL, more effective electron injection material is metal complex compounds and nitogen-contained heterocycle derivant.
As described metal complex compounds, such as oxine lithium, two (oxine) zinc, three (oxine) aluminium, three (oxine) gallium, two (10-hydroxy benzo [h] quinoline) beryllium, two (10-hydroxy benzo [h] quinoline) zinc etc. can be enumerated, but be not limited to these.
As described nitogen-contained heterocycle derivant, preferably such as oxazole, thiazole, oxadiazole, thiadiazoles, triazole, pyridine, pyrimidine, triazine, phenanthroline, benzoglyoxaline, imidazopyridine etc., wherein preferred benzimidizole derivatives, phenanthroline derivative, imidazopyridine derivatives.
As optimal way, also containing doping agent in these electron injection materials, in order to acceptant from the electronics of negative electrode, more preferably adulterating near the cathode interface of the 2nd organic layer with basic metal is the doping agent of representative.
As doping agent, can enumerate donor metal, donor metallic compound and donor metal complex, these reductibility doping agents can be used singly or in combination of two or more.
In above-mentioned organic EL, in luminescent layer, except at least one of the anthracene derivant represented except selecting free style (1), at least one of luminescent material, dopant material, hole-injecting material, hole mobile material and electron injection material can also be contained within the same layer.In addition, in order to improve the organic EL of gained relative to the stability of temperature, humidity, atmosphere etc., protective layer can also be set on the surface of element, or protect components integers by silicone oil, resin etc.
As the conductive material of the anode for above-mentioned organic EL, be suitably the material with the work function being greater than 4eV, can use carbon, aluminium, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium etc. and their alloy, for ito substrate, NESA substrate the metal oxide such as stannic oxide, Indium sesquioxide, also have the organic conductive such as Polythiophene, polypyrrole resin.As the conductive material for negative electrode, be suitably the material with the work function being less than 4eV, magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminium, lithium fluoride etc. and their alloy can be used, but be not limited to these.As alloy, magnesium/silver, magnesium/indium, lithium/aluminium etc. can be enumerated as representative examples, but be not limited to these.The ratio of alloy controls according to the temperature, atmosphere, vacuum tightness etc. of vapor deposition source, selects suitable ratio.Anode and negative electrode can be formed by two-layer above Rotating fields if needed.
In above-mentioned organic EL, in order to make its High Efficiency Luminescence, preferably make at least one side fully transparent in the emission wavelength region of element.In addition, preferable substrate is also transparent.Transparency electrode uses above-mentioned conductive material, utilizes the method such as vapour deposition method or sputtering method according to guaranteeing that the mode of the light transmission specified sets.Transmittance is preferably set to more than 10% by the electrode of light-emitting area.If substrate has physical strength, hot strength have the transparency, do not limit, have glass substrate and transparent resins film.
The formation of each layer of above-mentioned organic EL can apply the either method in the wet type membrane formation process such as dry type membrane formation process or spin-coating method, pickling process, flow coat method such as vacuum vapour deposition, sputtering method, plasma method, ion plating method.Thickness is not particularly limited, but needs to be set as suitable thickness.If thickness is blocked up, then needs large applying voltage to obtain certain optical output power, causing deterioration of efficiency thus.If thickness is crossed thin, produce pin hole etc., even if apply electric field can not obtain sufficient luminosity.Common thickness is suitably for the scope of 5nm ~ 10 μm, more preferably the scope of 10nm ~ 0.2 μm.
When wet type membrane formation process, will form the material dissolves of each layer or be scattered in the suitable solvent such as ethanol, chloroform, tetrahydrofuran (THF), diox and form film, this solvent can be any number of.
As the solution being applicable to such wet type membrane formation process, the solution containing organic EL Material of above-mentioned anthracene derivant and the solvent contained as organic EL Material can be used.
In any organic thin film layer, in order to improve film-forming properties, prevent the pin hole etc. of film, all can use suitable resin or additive.
Above-mentioned organic EL may be used for various electronics, may be used for the light source, display panel, mark lamp etc. of backlight or measuring instrument class etc. of the planar illuminant such as the flat-panel monitor of such as wall-hanging TV, duplicating machine, printer, liquid-crystal display.In addition, compound of the present invention not only may be used for organic EL, can also use in fields such as electrophotographic photoconductor, the components of photo-electric conversion, solar cell, image sensors.
Embodiment
Production Example 1 [synthesis of intermediate]
[chemical formula 81]
(1) synthesis of 5-bromo-2-fluorine iodobenzene
Under an argon, in 5-bromo-2-fluoroaniline 10g, add water 106mL stir, add concentrated hydrochloric acid 79.2mL.With frozen water cooling, drip the aqueous solution of Sodium Nitrite 4.36g.Stir 30 minutes under frozen water cooling after, add the aqueous solution of potassiumiodide 87.3g.After extracting by ethyl acetate, with saturated sodium bicarbonate aqueous solution, sodium sulfite aqueous solution washing organic layer, after dried over mgso, by solvent under reduced pressure distillation removing.To purify residue with silica gel column chromatography, obtain 5-bromo-2-fluorine iodobenzene 11.5g (yield 73%).
(2) synthesis of 3-methoxynaphthalene-2-boric acid
2-methoxynaphthalene 15.8g, tetrahydrofuran (THF) (dehydration) 300mL are added in flask, is cooled to-78 DEG C.(then (1.60M in hexane) 66mL, at room temperature stirs 4 hours to add n-BuLi wherein.Then be again cooled to-78 DEG C, add B (OMe) 327.3, stir at-78 DEG C after 10 minutes, at room temperature stir 5 hours.
After reaction terminates, add 1N HCl aq. (200mL), at room temperature stir 1 hour.Then be transferred to separating funnel, extract by ethyl acetate.
Use MgSO 4after this solution dry, concentrate, with hexanes wash, obtain the white solid 14.3g (yield 71%) of 3-methoxynaphthalene-2-boric acid.
(3) synthesis of 2-methoxyl group-3-(the fluoro-5-bromophenyl of 2-) naphthalene
Under an argon 3-methoxynaphthalene-2-boric acid 14.3g, 5-bromo-2-fluorine iodobenzene 21.3g, tetrakis triphenylphosphine palladium (0) 1.64g, toluene 220mL, 2M aqueous sodium carbonate 110mL are loaded flask, reflux stirs 8 hours.After cool to room temperature, use toluene extractive reaction solution, after removing water layer, wash organic layer with saturated brine.After dry over magnesium sulfate, concentrate, utilize silica gel column chromatography purification residue and obtain 2-methoxyl group-3-(the fluoro-5-bromophenyl of 2-) naphthalene 17.6g (yield 75%).
(4) synthesis of 2-hydroxyl-3-(the fluoro-5-bromophenyl of 2-) naphthalene
2-methoxyl group-3-(the fluoro-5-bromophenyl of 2-) naphthalene 15.8g, methylene dichloride (dehydration) 200mL are added in flask, is cooled to 0 DEG C.Add BBr 318.0g, then at room temperature stirs 24 hours.
After reaction terminates, solution is cooled to-78 DEG C, with methyl alcohol carefully by its inactivation, then with enough water inactivations.Solution is transferred to separating funnel, with dichloromethane extraction, uses MgSO 4after drying, carried out the removing of initial point impurity by short column of silica gel, concentrated solution, by the sample obtained vacuum-drying 5 hours thus obtain the white solid 15.1g of 2-hydroxyl-3-(the fluoro-5-bromophenyl of 2-) naphthalene at 60 DEG C.
(5) synthesis of intermediate (A)
By 2-hydroxyl-3-(the fluoro-5-bromophenyl of 2-) naphthalene 15.1g, METHYLPYRROLIDONE (dehydration) 150mL, K 2cO 313.2g adds in flask, then stirs 2 hours at 120 DEG C.
After reaction terminates, solution is cooled to room temperature, adds toluene (200mL), be transferred to separating funnel, wash with water.Use MgSO 4after this solution dry, utilize silica gel column chromatography purifying and the white solid 12.6g (yield 89%) that obtains as intermediate (A).
(6) synthesis of intermediate (B)
Intermediate (A) 12.6g, tetrahydrofuran (THF) (dehydration) 500mL are added in flask, is cooled to-78 DEG C.((1.60M in hexane) 28mL, while be warming up to 0 DEG C of limit to stir 2 hours to add n-BuLi wherein.Then be again cooled to-78 DEG C, add B (OMe) 311.6g, stir after 10 minutes at-78 DEG C, limit is slowly warming up to room temperature limit and stirs 5 hours.
After reaction terminates, add 1N HCl aq. (100mL), at room temperature stir 1 hour.Then be transferred to separating funnel, extract by ethyl acetate.
Use MgSO 4after this solution dry, concentrate, with hexanes wash, obtain the white solid 7.2g (yield 65%) as intermediate (B).
(7) synthesis of intermediate (C), intermediate (D)
[chemical formula 82]
In the synthesis of intermediate (A), (B), replace the 2-methoxynaphthalene of initial substance and use 1-methoxynaphthalene, using the same method synthetic intermediate (C), intermediate (D) according to above-mentioned route map.
(8) synthesis of intermediate (E)
[chemical formula 83]
Under an argon, intermediate (B) 2.88g, 4-bromo-iodobenzene 2.81g, tetrakis triphenylphosphine palladium (0) 0.231g, toluene 40mL, 2M aqueous sodium carbonate 20mL are loaded in flask, reflux stirs 8 hours.After being cooled to room temperature, with toluene extractive reaction solution, after removing water layer, wash organic layer with saturated brine.After dry over magnesium sulfate, concentrate, obtain intermediate (E) 3.16g (yield 85%) with silica gel column chromatography Purification.
(9) synthesis of intermediate (F)
[chemical formula 84]
In the synthesis of intermediate (E), replace 4-bromo-iodobenzene and use 3-bromo-iodobenzene to use the same method to synthesize.
(10) synthesis of intermediate (G)
[chemical formula 85]
In the synthesis of intermediate (E), replace intermediate (B) and use intermediate (D) to use the same method to synthesize.
(11) synthesis of intermediate (H)
[chemical formula 86]
In the synthesis of intermediate (E), replace intermediate (B) and use intermediate (D), replace 4-bromo-iodobenzene and use 3-bromo-iodobenzene to use the same method to synthesize.
(12) synthesis of intermediate (I), intermediate (J)
[chemical formula 87]
In the synthesis of intermediate (A), (B), replace the fluoro-5-bromo-iodobenzene of 2-and use the fluoro-4-bromo-iodobenzene of 2-, to use the same method synthetic intermediate (I), intermediate (J) according to above-mentioned schema.
(13) synthesis of intermediate (K), intermediate (L)
[chemical formula 88]
In the synthesis of intermediate (A), (B), replace 2-methoxynaphthalene and use 1-methoxynaphthalene, replace the fluoro-5-bromo-iodobenzene of 2-and use the fluoro-4-bromo-iodobenzene of 2-, to use the same method synthetic intermediate (K), intermediate (L) according to above-mentioned schema.
(14) synthesis of intermediate (M)
[chemical formula 89]
In the synthesis of intermediate (E), replace intermediate (B) and use intermediate (J) to use the same method to synthesize, obtain intermediate (M).
(15) synthesis of intermediate (N)
[chemical formula 90]
In the synthesis of intermediate (E), replace intermediate (B) and use intermediate (L) to use the same method to synthesize, obtain intermediate (N).
Embodiment 1 [synthesis of anthracene derivant (compound 1)]
[chemical formula 91]
Under an argon, 10-phenylanthracene-9-boric acid the 3.28g, tetrakis triphenylphosphine palladium (0) 0.231g, 1 that load intermediate (A) 2.96g, synthesize with currently known methods, 2-glycol dimethyl ether 20mL, toluene 20mL, 2M aqueous sodium carbonate 20mL, return stirring 8 hours.After being cooled to room temperature, filter the solid of separating out.After the solid obtained by water, methanol wash, carry out recrystallization with toluene, obtain the faint yellow solid 4.04g of compound 1.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 470.17, m/e=470.
Embodiment 2 [synthesis of anthracene derivant (compound 2)]
[chemical formula 92]
In the synthesis of the compound 1 of embodiment 1, using except 10-(1-naphthyl) anthracene-9-boric acid utilizing currently known methods to synthesize except replacing 10-phenylanthracene-9-boric acid, similarly synthesizing, obtaining compound 2.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 520.18, m/e=520.
Embodiment 3 [synthesis of anthracene derivant (compound 3)]
[chemical formula 93]
In the synthesis of the compound 1 of embodiment 1, using except replacing 10-phenylanthracene-9-boric acid except 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, similarly synthesizing, obtaining compound 3.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 520.18, m/e=520.
Embodiment 4 [synthesis of anthracene derivant (compound 4)]
[chemical formula 94]
In the synthesis of the compound 1 of embodiment 1, using except replacing 10-phenylanthracene-9-boric acid except 10-(4-xenyl) anthracene-9-boric acid according to currently known methods synthesis, similarly synthesizing, obtaining compound 4.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 546.20, m/e=546.
Embodiment 5 [synthesis of anthracene derivant (compound 5)]
[chemical formula 95]
In the synthesis of the compound 1 of embodiment 1, using except replacing 10-phenylanthracene-9-boric acid except 10-(3-xenyl) anthracene-9-boric acid according to currently known methods synthesis, similarly synthesizing, obtaining compound 5.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 546.20, m/e=546.
Embodiment 6 [synthesis of anthracene derivant (compound 6)]
[chemical formula 96]
In the synthesis of the compound 1 of embodiment 1, using except replacing 10-phenylanthracene-9-boric acid except 10-[4-(1-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, similarly synthesizing, obtaining compound 6.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 7 [synthesis of anthracene derivant (compound 7)]
[chemical formula 97]
In the synthesis of the compound 1 of embodiment 1, using except replacing 10-phenylanthracene-9-boric acid except 10-[3-(1-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, similarly synthesizing, obtaining compound 7.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 8 [synthesis of anthracene derivant (compound 8)]
[chemical formula 98]
In the synthesis of the compound 1 of embodiment 1, using except replacing 10-phenylanthracene-9-boric acid except 10-[4-(2-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, similarly synthesizing, obtaining compound 8.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 9 [synthesis of anthracene derivant (compound 9)]
[chemical formula 99]
In the synthesis of the compound 1 of embodiment 1, using except replacing 10-phenylanthracene-9-boric acid except 10-[3-(2-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, similarly synthesizing, obtaining compound 9.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 10 [synthesis of anthracene derivant (compound 10)]
[chemical formula 100]
In the synthesis of the compound 1 of embodiment 1, using except replacing 10-phenylanthracene-9-boric acid except 10-(2-dibenzofuran group) anthracene-9-boric acid according to currently known methods synthesis, similarly synthesizing, obtaining compound 10.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 560.64, m/e=560.
Embodiment 11 [synthesis of anthracene derivant (compound 11)]
[chemical formula 101]
In the synthesis of the compound 1 of embodiment 1, use except 10-[3-(9-phenyl) carbazyl] anthracene-9-boric acid according to currently known methods synthesis except replacing 10-phenylanthracene-9-boric acid, similarly synthesize, obtain compound 11.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 635.22, m/e=635.
Embodiment 12 [synthesis of anthracene derivant (compound 12)]
[chemical formula 102]
In the synthesis of the compound 1 of embodiment 1, using except intermediate (E) except replacing intermediate (A), similarly synthesizing, obtaining compound 12.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 546.20, m/e=546.
Embodiment 13 [synthesis of anthracene derivant (compound 13)]
[chemical formula 103]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (E), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 13.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 14 [synthesis of anthracene derivant (compound 14)]
[chemical formula 104]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (E), replace 10-phenylanthracene-9-boric acid and use 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 14.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 15 [synthesis of anthracene derivant (compound 15)]
[chemical formula 105]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (E), replace 10-phenylanthracene-9-boric acid and use 10-(4-xenyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 15.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 622.23, m/e=622.
Embodiment 16 [synthesis of anthracene derivant (compound 16)]
[chemical formula 106]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (E), replace 10-phenylanthracene-9-boric acid and use 10-(3-xenyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 16.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 622.23, m/e=622.
Embodiment 17 [synthesis of anthracene derivant (compound 17)]
[chemical formula 107]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (E), replace 10-phenylanthracene-9-boric acid and use 10-[4-(1-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 17.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 672.25, m/e=672.
Embodiment 18 [synthesis of anthracene derivant (compound 18)]
[chemical formula 108]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (E), replace 10-phenylanthracene-9-boric acid and use 10-[3-(1-naphthyl) phenyl] anthracene-9-boric acid utilizing currently known methods to synthesize, in addition similarly synthesize, obtain compound 18.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 672.25, m/e=672.
Embodiment 19 [synthesis of anthracene derivant (compound 19)]
[chemical formula 109]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (E), replace 10-phenylanthracene-9-boric acid and use 10-[4-(2-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 19.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 672.25, m/e=672.
Embodiment 20 [synthesis of anthracene derivant (compound 20)]
[chemical formula 110]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (E), replace 10-phenylanthracene-9-boric acid and use 10-[3-(2-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 20.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 672.25, m/e=672.
Embodiment 21 [synthesis of anthracene derivant (compound 21)]
[chemical formula 111]
In the synthesis of the compound 1 of embodiment 1, use except intermediate (F) except replacing intermediate (A) and similarly synthesize, obtain compound 21.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 546.20, m/e=546.
Embodiment 22 [synthesis of anthracene derivant (compound 22)]
[chemical formula 112]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (F), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 22.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 23 [synthesis of anthracene derivant (compound 23)]
[chemical formula 113]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (F), replace 10-phenylanthracene-9-boric acid and use 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 23.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 24 [synthesis of anthracene derivant (compound 24)]
[chemical formula 114]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (F), replace 10-phenylanthracene-9-boric acid and use 10-(4-xenyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 24.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 622.23, m/e=622.
Embodiment 25 [synthesis of anthracene derivant (compound 25)]
[chemical formula 115]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (F), replace 10-phenylanthracene-9-boric acid and use 10-(3-xenyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 25.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 622.23, m/e=622.
Embodiment 26 [synthesis of anthracene derivant (compound 26)]
[chemical formula 116]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (F), replace 10-phenylanthracene-9-boric acid and use 10-[4-(1-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 26.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 672.25, m/e=672.
Embodiment 27 [synthesis of anthracene derivant (compound 27)]
[chemical formula 117]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (F), replace 10-phenylanthracene-9-boric acid and use 10-[3-(1-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 27.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 672.25, m/e=672.
Embodiment 28 [synthesis of anthracene derivant (compound 28)]
[chemical formula 118]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (F), replace 10-phenylanthracene-9-boric acid and use 10-[4-(2-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 28.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 672.25, m/e=672.
Embodiment 29 [synthesis of anthracene derivant (compound 29)]
[chemical formula 119]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (F), replace 10-phenylanthracene-9-boric acid and use 10-[3-(2-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 29.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 672.25, m/e=672.
Embodiment 30 [synthesis of anthracene derivant (compound 30)]
[chemical formula 120]
In the synthesis of the compound 1 of embodiment 1, use except intermediate (C) except replacing intermediate (A) and similarly synthesize, obtain compound 30.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 470.17, m/e=470.
Embodiment 31 [synthesis of anthracene derivant (compound 31)]
[chemical formula 121]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (C), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 31.This compound is target compound by the result of mass spectroscopy, relative molecular weight 520.18, m/e=520.
Embodiment 32 [synthesis of anthracene derivant (compound 32)]
[chemical formula 122]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (C), replace 10-phenylanthracene-9-boric acid and use 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 32.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 520.18, m/e=520.
Embodiment 33 [synthesis of anthracene derivant (compound 33)]
[chemical formula 123]
In the synthesis of the compound 1 of embodiment 1, use except intermediate (H) except replacing intermediate (A) and similarly synthesize, obtain compound 33.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 546.20, m/e=546.
Embodiment 34 [synthesis of anthracene derivant (compound 34)]
[chemical formula 124]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (H), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 34.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 35 [synthesis of anthracene derivant (compound 35)]
[chemical formula 125]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (H), replace 10-phenylanthracene-9-boric acid and use 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 35.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 36 [synthesis of anthracene derivant (compound 36)]
[chemical formula 126]
In the synthesis of the compound 1 of embodiment 1, use except intermediate (G) except replacing intermediate (A) and similarly synthesize, obtain compound 36.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 546.20, m/e=546.
Embodiment 37 [synthesis of anthracene derivant (compound 37)]
[chemical formula 127]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (G), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 37.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 38 [synthesis of anthracene derivant (compound 38)]
[chemical formula 128]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (G), replace 10-phenylanthracene-9-boric acid and use 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 38.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 39 [synthesis of anthracene derivant (compound 39)]
[chemical formula 129]
In the synthesis of the compound 1 of embodiment 1, use except intermediate (I) except replacing intermediate (A) and similarly synthesize, obtain compound 39.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 470.17, m/e=470.
Embodiment 40 [synthesis of anthracene derivant (compound 40)]
[chemical formula 130]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (I), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 40.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 520.62, m/e=520.
Embodiment 41 [synthesis of anthracene derivant (compound 41)]
[chemical formula 131]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (I), replace 10-phenylanthracene-9-boric acid and use 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 41.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 520.62, m/e=520.
Embodiment 42 [synthesis of anthracene derivant (compound 42)]
[chemical formula 132]
In the synthesis of the compound 1 of embodiment 1, use except intermediate (M) except replacing intermediate (A) and similarly synthesize, obtain compound 42.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 546.20, m/e=546.
Embodiment 43 [synthesis of anthracene derivant (compound 43)]
[chemical formula 133]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (M), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 43.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 44 [synthesis of anthracene derivant (compound 44)]
[chemical formula 134]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (M), replace 10-phenylanthracene-9-boric acid and use 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 44.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 45 [synthesis of anthracene derivant (compound 45)]
[chemical formula 135]
In the synthesis of the compound 1 of embodiment 1, use except intermediate (K) except replacing intermediate (A) and similarly synthesize, obtain compound 45.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 470.17, m/e=470.
Embodiment 46 [synthesis of anthracene derivant (compound 46)]
[chemical formula 136]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (K), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 46.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 520.18, m/e=520.
Embodiment 47 [synthesis of anthracene derivant (compound 47)]
[chemical formula 137]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (K), replace 10-phenylanthracene-9-boric acid and use 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 47.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 520.18, m/e=520.
Embodiment 48 [synthesis of anthracene derivant (compound 48)]
[chemical formula 138]
In the synthesis of the compound 1 of embodiment 1, use except intermediate (N) except replacing intermediate (A) and similarly synthesize, obtain compound 48.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 546.20, m/e=546.
Embodiment 49 [synthesis of anthracene derivant (compound 49)]
[chemical formula 139]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (N), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 49.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 50 [synthesis of anthracene derivant (compound 50)]
[chemical formula 140]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (N), replace 10-phenylanthracene-9-boric acid and use 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 50.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Production Example 2 [synthesis of intermediate]
(1) synthesis of intermediate (O), (P)
[chemical formula 141]
In the synthesis of intermediate (A), (B), replace the 2-methoxynaphthalene of initial substance and use 9-methoxyl group luxuriant and rich with fragrance, using the same method synthetic intermediate (O), intermediate (P) according to above-mentioned schema.
(2) synthesis of intermediate (Q)
[chemical formula 142]
In the synthesis of intermediate (E), replace intermediate (B) and use intermediate (P) to use the same method to synthesize, obtain intermediate (Q).
Embodiment 51 [synthesis of anthracene derivant (compound 51)]
[chemical formula 143]
In the synthesis of the compound 1 of embodiment 1, use except intermediate (O) except replacing intermediate (A) and similarly synthesize, obtain compound 51.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 520.18, m/e=520.
Embodiment 52 [synthesis of anthracene derivant (compound 52)]
[chemical formula 144]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (O), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 52.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 570.20, m/e=570.
Embodiment 53 [synthesis of anthracene derivant (compound 53)]
[chemical formula 145]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (O), replace 10-phenylanthracene-9-boric acid and use 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 53.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 570.20, m/e=570.
Embodiment 54 [synthesis of anthracene derivant (compound 54)]
[chemical formula 146]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (O), replace 10-phenylanthracene-9-boric acid and use 10-(4-xenyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 54.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=570.
Embodiment 55 [synthesis of anthracene derivant (compound 55)]
[chemical formula 147]
In the synthesis of the compound 1 of embodiment 1, use except intermediate (Q) except replacing intermediate (A) and similarly synthesize, obtain compound 55.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 56 [synthesis of anthracene derivant (compound 56)]
[chemical formula 148]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (Q), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 56.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 646.23, m/e=646.
Embodiment 57 [synthesis of anthracene derivant (compound 57)]
[chemical formula 149]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (Q), replace 10-phenylanthracene-9-boric acid and use 10-(2-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 57.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 646.23, m/e=646.
Embodiment 58 [synthesis of anthracene derivant (compound 58)]
[chemical formula 150]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (Q), replace 10-phenylanthracene-9-boric acid and use 10-(4-xenyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 58.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 672.25, m/e=672.
Production Example 3 [synthesis of intermediate]
(1) synthesis of intermediate (R), (S)
[chemical formula 151]
In the synthesis of intermediate (A), (B), replace 2-methoxynaphthalene and use 9-methoxyl group luxuriant and rich with fragrance, replace the fluoro-5-bromo-iodobenzene of 2-and use the fluoro-4-bromo-iodobenzene of 2-, to use the same method synthetic intermediate (R), intermediate (S) according to above-mentioned schema.
(2) synthesis of intermediate (T)
[chemical formula 152]
In the synthesis of intermediate (E), replace intermediate (B) and use intermediate (S) to use the same method to synthesize, obtain intermediate (T).
Embodiment 59 [synthesis of anthracene derivant (compound 59)]
[chemical formula 153]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (R), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 59.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 570.20, m/e=570.
Embodiment 60 [synthesis of anthracene derivant (compound 60)]
[chemical formula 154]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (T), replace 10-phenylanthracene-9-boric acid and use 10-(1-naphthyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 60.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 646.23, m/e=646.
Embodiment 61 [synthesis of anthracene derivant (compound 61)]
[chemical formula 155]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (C), replace 10-phenylanthracene-9-boric acid and use 10-(4-xenyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 61.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 546.20, m/e=546.
Embodiment 62 [synthesis of anthracene derivant (compound 62)]
[chemical formula 156]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (C), replace 10-phenylanthracene-9-boric acid and use 10-(3-xenyl) anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 62.This compound is target compound by the result of mass spectroscopy, obtains molecular weight 546.20, m/e=546.
Embodiment 63 [synthesis of anthracene derivant (compound 63)]
[chemical formula 157]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (C), replace 10-phenylanthracene-9-boric acid and use 10-[4-(1-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 63.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 64 [synthesis of anthracene derivant (compound 64)]
[chemical formula 158]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (C), replace 10-phenylanthracene-9-boric acid and use 10-[4-(2-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 64.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 65 [synthesis of anthracene derivant (compound 65)]
[chemical formula 159]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (C), replace 10-phenylanthracene-9-boric acid and use 10-[3-(1-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 65.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 66 [synthesis of anthracene derivant (compound 66)]
[chemical formula 160]
In the synthesis of the compound 1 of embodiment 1, replace intermediate (A) and use intermediate (C), replace 10-phenylanthracene-9-boric acid and use 10-[3-(2-naphthyl) phenyl] anthracene-9-boric acid according to currently known methods synthesis, in addition similarly synthesize, obtain compound 66.This compound is target compound by the result of mass spectroscopy, relative to molecular weight 596.21, m/e=596.
Embodiment 67
After the glass substrate with ito transparent electrode (anode) (lucky Olympic Equestrian Company system) thick for 25mm × 75mm × 1.1mm is carried out 5 minutes ultrasonic washings in Virahol, carry out 30 minutes UV ozone washing.The glass substrate with transparent electrode lines after washing is contained on the frame substrate of vacuum deposition apparatus, first on the face of side being formed with transparent electrode lines according to the compound H AT of mode film forming thickness 5nm covering described transparency electrode.After the film forming of HAT film, the HT1 of film forming thickness 80nm on this HAT film.After the film forming of HT1 film, the HT2 of film forming thickness 15nm on this HT1 film.
On HT2 film, by the BH1 (compound 4) of manufacture in embodiment 4 and doping agent BD1 with the Film Thickness Ratio film forming of 19:1, as the blue series luminescent layer of thickness 25nm.
On luminescent layer with thickness 20nm evaporation ET1 and film forming using as electron transfer layer.After the film forming of ET1 film, the ET2 of film forming thickness 5nm on this ET1 film.Then, by LiF with thickness 1nm film forming.On this LiF film, evaporation 80nm metal A l forms metallic cathode and forms organic EL luminous element.
For the organic EL made as above, measure voltage and external quantum efficiency (EQE).Measure in the following manner specifically.Result is shown in table 1.
Driving voltage
Measure and become 10mA/cm according to current density 2the voltage (unit: V) of mode when being energized between ito transparent electrode and metal A l negative electrode.
External quantum efficiency EQE
By spectroradio luminance spectral, assuming that carried out Lang Bote (Lanbertian) radiation and calculated external quantum efficiency EQE (unit: %).
Comparative example 1
In the film forming of luminescent layer, use except BH2 except replacing BH1 and form organic EL luminous element in the same manner as embodiment 67, evaluate.Result is shown in table 1.
The compound used in embodiment and comparative example illustrates below.
[chemical formula 161]
[table 1]
Luminescent layer host compound Voltage (V) EQE(％)
Embodiment 67 BH1 3.4 9.26
Comparative example 1 BH2 3.6 8.96
Known by the above results, in the embodiment 67 of use compd B H1 of the present invention, the group that through type (2) represents and anthracene skeleton at specific position bonding, thus compared with using the comparative example 1 of compd B H2, achieve lower voltage, high efficiency.Infer that this is the expansion due to the planarity by molecule, intermolecular fillibility improves, and electron injection, transmittability improve.
Embodiment 68
After the glass substrate with ito transparent electrode (anode) (lucky Olympic Equestrian Company system) thick for 25mm × 75mm × 1.1mm is carried out 5 minutes ultrasonic washings in Virahol, carry out 30 minutes UV ozone washing.The glass substrate with transparent electrode lines after washing is contained on the frame substrate of vacuum deposition apparatus, first on the face of side being formed with transparent electrode lines according to the compound H AT of mode film forming thickness 5nm covering described transparency electrode.After the film forming of HAT film, the HT3 of film forming thickness 80nm on this HAT film.After the film forming of HT3 film, the HT4 of film forming thickness 15nm on this HT3 film.
On HT4 film, by embodiment 1 manufacture compound 1 and doping agent BD1 with the Film Thickness Ratio film forming of 19:1, as the blue series luminescent layer of thickness 25nm.
On luminescent layer as electron transfer layer with thickness 20nm evaporation ET1 thus film forming.After the film forming of ET1 film, by the ET3 film forming of thickness 5nm.Then, by LiF with thickness 1nm film forming.On this LiF film, evaporation 80nm metal A l forms metallic cathode and forms organic EL luminous element.
Organic EL luminous element is evaluated in the same manner as embodiment 67.Result is shown in table 2.
Embodiment 69 ~ 88, comparative example 2,3
In the film forming of luminescent layer, using except compound shown in table 2 except replacing compound 1, forming organic EL luminous element in the same manner as embodiment 68, evaluating.Result is shown in table 2.
The compound used in embodiment and comparative example illustrates below.
[chemical formula 162]
[table 2]
Luminescent layer host compound Voltage (V) EQE(％)
Embodiment 68 Compound 1 3.9 9.1
Embodiment 69 Compound 2 3.8 9.2
Embodiment 70 Compound 3 3.8 9.2
Embodiment 71 Compound 4 3.8 9.0
Embodiment 72 Compound 5 3.9 9.2
Embodiment 73 Compound 6 3.8 9.0
Embodiment 74 Compound 7 3.9 8.9
Embodiment 75 Compound 8 3.8 9.0
Embodiment 76 Compound 9 3.9 8.9
Embodiment 77 Compound 10 4.0 9.2
Embodiment 78 Compound 23 4.0 8.9
Embodiment 79 Compound 30 4.1 8.9
Embodiment 80 Compound 31 4.0 8.8
Embodiment 81 Compound 32 4.0 8.9
Embodiment 82 Compound 52 4.1 8.6
Embodiment 83 Compound 61 4.0 8.9
Embodiment 84 Compound 62 4.1 8.9
Embodiment 85 Compound 63 4.0 8.8
Embodiment 86 Compound 64 4.0 8.9
Embodiment 87 Compound 65 4.1 8.8
Embodiment 88 Compound 66 4.1 8.9
Comparative example 2 BH3 4.4 8.1
Comparative example 3 BH4 4.4 4.9
Known compared with using the comparative example 2 of compd B H3, use the embodiment 68 ~ 88 of compound of the present invention to achieve lower voltage, high efficiency.As its reason, as described above, supposition is that intermolecular fillibility improves due to the expansion of the planarity by molecule, and electron injection, transmittability improve.
In addition, known embodiment 68 ~ 88 achieves lower voltage compared with using the comparative example 3 of compd B H4, and significantly high efficiency.As its reason, supposition is because the specific bonding position on anthracene skeleton makes the planarity of molecule expand, and electron injection, transmittability improve as described above.
Several embodiment of the present invention and/or embodiment is described in detail above, but to those skilled in the art, when easily substantially not departing from new enlightenment of the present invention and effect, to as these illustrative embodiments and/or embodiment in addition numerous variations.Therefore, these numerous variations within the scope of the present invention.
The content of the Japanese patent application specification sheets on the basis of Paris preference as the application is all incorporated herein.

Claims (22)

1. an anthracene derivant, it is represented by following formula (1),
In formula (1), R 1~ R 8be selected from respectively hydrogen atom, halogen atom, hydroxyl, cyano group, replacement or without the amino replaced, replacement or without the carbon number replaced be 1 ~ 20 alkyl, replacement or without the carbon number replaced be 1 ~ 20 alkoxyl group, replacement or without arylthio, replacement or the carbon number without the formation ring replaced that aryloxy, replacement or the carbon number without the formation ring replaced that the carbon number of formation ring replaced is 6 ~ 30 are 6 ~ 30 be 6 ~ 30 aryl and replacement or the atomicity without the formation ring replaced be the heterocyclic radical of 5 ~ 30
L 1be selected from singly-bound and linking group, described linking group is selected from the arylidene of divalent and the heterocyclic radical of divalent,
Ar 1be selected from following formula (2) and (3),
In formula (2), (3), X is selected from Sauerstoffatom and sulphur atom,
In formula (2), R 11~ R 14in any one for L 1bonding, not for L 1the R of bonding 11~ R 14and R 15~ R 20be selected from R respectively 1~ R 8the group of middle definition or atom,
In formula (3), R 21~ R 24in any one for L 1bonding, not for L 1the R of bonding 21~ R 24and R 25~ R 30be selected from R respectively 1~ R 8the group of middle definition or atom,
Ar 2be selected from replace or without the carbon number of formation ring replaced be 6 ~ 50 aryl and replacement or the atomicity without the formation ring replaced be the heterocyclic radical of 5 ~ 50,
R 1~ R 8, R 11~ R 20, R 21~ R 30, L 1and Ar 2in the adjacent optional bonding mutually of group and form ring.
2. anthracene derivant as claimed in claim 1, it is represented by one of any in following formula (4) ~ (7),
In formula (4) ~ (7), R 1~ R 8, L 1, X, R 11~ R 20, R 21~ R 30and Ar 2identical with above-mentioned formula (1).
3. anthracene derivant as claimed in claim 1 or 2, it is represented by one of any in following formula (8) ~ (11),
In formula (8) ~ (11), R 1~ R 8, X, R 11~ R 20, R 21~ R 30and Ar 2identical with above-mentioned formula (1).
4. anthracene derivant as claimed in claim 1 or 2, it is represented by one of any in following formula (12) ~ (15),
In formula (12) ~ (15), R 1~ R 8, X, R 11~ R 20, R 21~ R 30and Ar 2identical with above-mentioned formula (1).
5. the anthracene derivant according to any one of Claims 1 to 4, wherein,
Ar 2be selected from replace or without replace phenyl, replacement or without replace naphthyl, replacement or without replace phenanthryl, replacement or without replace benzo anthryl, replacement or without replace 9,9-dimethyl fluorenyls and replacement or without replace dibenzofuran group.
6. the anthracene derivant according to any one of Claims 1 to 5, wherein, R 1~ R 8for hydrogen atom.
7. the anthracene derivant according to any one of claim 1 ~ 6, wherein, not for L 1the R of bonding 11~ R 14and R 15~ R 20, and not for L 1the R of bonding 21~ R 24and R 25~ R 30for hydrogen atom.
8. the anthracene derivant according to any one of claim 1 ~ 7, wherein, X is Sauerstoffatom.
9. the anthracene derivant according to any one of claim 1 ~ 8, it is material for organic electroluminescence device.
10. the anthracene derivant according to any one of claim 1 ~ 9, it is organic electroluminescent device luminescent material.
11. 1 kinds of organic electroluminescent devices, it is clamped with the organic thin film layer of more than 1 layer that comprises luminescent layer between negative electrode and positive electrode, and at least one deck of described organic thin film layer contains separately or contains the anthracene derivant according to any one of claim 1 ~ 10 as the ingredients of a mixture.
12. organic electroluminescent devices as claimed in claim 11, wherein, described luminescent layer contains described anthracene derivant.
13. organic electroluminescent devices as claimed in claim 12, wherein, described anthracene derivant is material of main part.
14. organic electroluminescent devices as described in claim 12 or 13, wherein, described luminescent layer is also containing dopant material.
15. organic electroluminescent devices as claimed in claim 14, wherein, described dopant material is novel arylamine compound.
16. organic electroluminescent devices as claimed in claim 14, wherein, described dopant material is styrylamine compounds.
17. organic electroluminescent devices as claimed in claim 15, wherein, described dopant material is the fused polycycle sulfonamide derivatives shown in following formula (20),
In formula (20), Y be replace or without the carbon number of formation ring replaced be 10 ~ 50 fused aromatic alkyl,
Ar 101and Ar 102be selected from respectively replace or without the carbon number of formation ring replaced be 6 ~ 50 aryl and replacement or the atomicity without the formation ring replaced be the heterocyclic radical of 5 ~ 50,
N is the integer of 1 ~ 4.
18. organic electroluminescent devices as claimed in claim 15, wherein, described dopant material is the fused polycycle sulfonamide derivatives shown in following formula (21),
In formula (21), R ebe selected from respectively replace or without replace carbon number be the alkyl of 1 ~ 20, replacement or the carbon number without replacement are the thiazolinyl of 2 ~ 50, replacement or the carbon number without replacement are the alkynyl of 2 ~ 50, replacement or the carbon number without replacement are the aralkyl of 1 ~ 20, replacement or the carbon number without the formation ring replaced are the cycloalkyl of 3 ~ 20, replacement or the carbon number without replacement are the alkoxyl group of 1 ~ 20, replacement or the carbon number without the formation ring replaced are the aryloxy of 6 ~ 20, replacement or the carbon number without the formation ring replaced are the aryl of 6 ~ 50, replacement or the silyl without replacement, replace or without replace carbon number be 1 ~ 50 alkyl germanium base, and replace or without the carbon number of formation ring replaced be 6 ~ 50 aryl germanium base, R eoptionally be bonded to any bonding position of 4 phenyl ring of fused polycycle,
T is the integer of 0 ~ 10,
Ar 201~ Ar 204be selected from respectively replace or without the carbon number of formation ring replaced be 6 ~ 50 aryl and replacement or the atomicity without the formation ring replaced be the heterocyclic radical of 5 ~ 50.
19. organic electroluminescent devices as claimed in claim 15, wherein, described dopant material is the fused polycycle sulfonamide derivatives shown in following formula (22),
In formula (22), R fbe selected from respectively replace or without replace carbon number be the alkyl of 1 ~ 20, replacement or the carbon number without replacement are the thiazolinyl of 2 ~ 50, replacement or the carbon number without replacement are the alkynyl of 2 ~ 50, replacement or the carbon number without replacement are the aralkyl of 1 ~ 20, replacement or the carbon number without the formation ring replaced are the cycloalkyl of 3 ~ 20, replacement or the carbon number without replacement are the alkoxyl group of 1 ~ 20, replacement or the carbon number without the formation ring replaced are the aryloxy of 6 ~ 20, replacement or the carbon number without the formation ring replaced are the aryl of 6 ~ 50, replacement or the silyl without replacement, replace or without replace carbon number be 1 ~ 50 alkyl germanium base, and replace or without the carbon number of formation ring replaced be 6 ~ 50 aryl germanium base, R foptionally be bonded to any bonding position of 4 phenyl ring of fused polycycle,
U is the integer of 0 ~ 8,
Ar 205~ Ar 208be selected from respectively and replace or be the aryl of 6 ~ 50 without the carbon number of formation ring replaced and replace or atomicity without the formation ring replaced is the heterocyclic radical of 5 ~ 50.
20. organic electroluminescent devices as claimed in claim 15, wherein, described dopant material is the fused polycycle sulfonamide derivatives shown in following formula (23),
In formula (23), R gbe selected from respectively replace or without replace carbon number be the alkyl of 1 ~ 20, replacement or the carbon number without replacement are the thiazolinyl of 2 ~ 50, replacement or the carbon number without replacement are the alkynyl of 2 ~ 50, replacement or the carbon number without replacement are the aralkyl of 1 ~ 20, replacement or the carbon number without the formation ring replaced are the cycloalkyl of 3 ~ 20, replacement or the carbon number without replacement are the alkoxyl group of 1 ~ 20, replacement or the carbon number without the formation ring replaced are the aryloxy of 6 ~ 20, replacement or the carbon number without the formation ring replaced are the aryl of 6 ~ 50, replacement or the silyl without replacement, replace or without replace carbon number be 1 ~ 50 alkyl germanium base, and replace or without the carbon number of formation ring replaced be 6 ~ 50 aryl germanium base, R goptionally be bonded to any bonding position of 3 phenyl ring of fused polycycle,
M is the integer of 0 ~ 10,
Ar 209~ Ar 212be selected from respectively and replace or be the aryl of 6 ~ 50 without the carbon number of formation ring replaced and replace or atomicity without the formation ring replaced is the heterocyclic radical of 5 ~ 50.
21. organic electroluminescent devices as claimed in claim 15, wherein, described dopant material is the fused polycycle sulfonamide derivatives shown in following formula (24),
In formula (24), Ar 213~ Ar 218be selected from respectively replace or without the carbon number of formation ring replaced be 6 ~ 50 aryl and replacement or the atomicity without the formation ring replaced be the heterocyclic radical of 5 ~ 50.
22. 1 kinds of electronicss, it comprises the organic electroluminescent device according to any one of claim 11 ~ 21.
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CN107925007A (en) * 2015-08-12 2018-04-17 默克专利有限公司 material for electronic device
CN108164462A (en) * 2018-02-08 2018-06-15 烟台显华化工科技有限公司 One kind is used as nitrogen-containing heterocycle compound and the application of luminescent material
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